Field of the invention
[0001] The present invention relates to a softener composition, more particularly to a liquid
softener composition and a method for producing the same.
Background of the invention
[0002] Conventionally, a di-long chain alkyl ester or a di-short chain alkyl quaternary
ammonium salt is used as a softener composition to soften fabrics. However, techniques
of adding various additives and using a base to which an alkenyl group is introduced
in order to yield the softness , water absorption and dispersibility of softeners
have been known (for example, refer to
JP-A 7-18575,
JP-A 2001-192966, and
JP-A2003-519294).
WO 01/02338 is directed to a fabric care composition containing a fabric softening active and
a carrier. The fabric softening active may contain a mixture of quaternary nitrogen
compounds of a specific formula, having alkyl residues and/or acylated (poly) oxyalkylene
residues attached to the nitrogen atom.
WO 95/20640 concerns detergent mixtures containing esterquats and soil-release polymers. The
mixtures are said to achieve a synergistic improvement in softness of texture and
rewettability from a large number of materials. Materials pretreated with the detergent
mixtures proposed soil less heavily and can also be more easily freed from oil-containing
soiling. The mixtures are suitable for use in, for instance, the preparation of fabric
softeners and hair shampoos.
Summary of the Invention
[0003] The present invention relates to a softener composition, comprising a quaternary
ammonium salt represented by formula (I) :

wherein R
1 and R
2 may be the same as or different from each other and represent a hydrocarbon group
having 11 to 23 carbon atoms, R
3 and R
4 may be the same as or different from each other and represent a hydrocarbon group
having 1 to 4 carbon atoms, k and 1 may be the same as or different from each other
and represent an integer of 5 to 10 and X
- represents an anion.
[0004] In another aspect, the present invention relates to the above softener composition,
further further comprising a quaternary ammonium salt represented by formula (II):

wherein R
5 and R
6 may be the same as or different from each other and represent a hydrocarbon group
having 11 to 23 carbon atoms, R
7 and R
8 may be the same as or different from each other and represent a hydrocarbon group
having 1 to 4 carbon atoms which may have a hydroxyl group, m and n may be the same
as or different from each other and represent an integer of 2 or 3 and X'
- represents an anion.
[0005] The present invention relates to a method for producing the softener composition
of the above shown invention composition, including the following steps 1 and 2 as
a step of producing the quaternary ammonium salt represented by the formula (I):
step 1: producing a bis(polyalkoxyalkanol)alkylamine by a reaction of a halopoly alkoxy
alkanol with an amine represented by the following formula (III):
R3-NH2 (III)
[wherein R3 represents a hydrocarbon group having 1 to 4 carbon atoms.]; and
step 2: esterifying the bis(polyalkoxyalkanol)alkylamine produced in the step 1 with
fatty acids or a derivative thereof and quaternizing the ester.
[0006] The present invention relates to use of the quaternary ammonium salt (I) for softener.
The present invention relates to use of the composition containing the quaternary
ammonium salt (I) and the quaternary ammonium salt (II) for softener.
Detailed description of the invention
[0008] The present invention provides a softener composition having excellent handling properties
such that compatibility between a good softness and water absorption which is usually
considered to be difficult is ensured, while exhibiting good softness, and good component
dispersibility is exhibited without causing sequential thickening, more particularly
a liquid softener composition.
[0009] According to the present invention, there is provided a softener composition having
excellent handling properties such that compatibility between good softness and water
absorption which is usually considered to be difficult is ensured, while exhibiting
good softness, and good component dispersibility is exhibited without causing sequential
thickening, more particularly a liquid softener composition.
<Quaternary ammonium salt (I)>
[0010] The quaternary ammonium salt (I) is a compound represented by the formula (I). From
the viewpoint of softness, R
1 and R
2 in the formula (I) are a hydrocarbon group having 11 to 23 carbon atoms, preferably
15 to 21 carbon atoms, more preferably 15 to 17 carbon atoms, and are preferably an
alkyl group or an alkenyl group. Specific examples thereof include various kinds of
undecyl groups, various kinds of dodecyl groups, various kinds of tridecyl groups,
various kinds of tetradecyl groups, various kinds of pentadecyl groups, various kinds
of hexadecyl groups, various kinds of heptadecyl groups, various kinds of octadecyl
groups, various kinds of nonadecyl groups, various kinds of eicosanyl groups, various
kinds of heneicosanyl groups, various kinds of docosanyl groups, various kinds of
tricosanyl groups, various kinds of undecenyl groups, various kinds of dodecenyl groups,
various kinds of tridecenyl groups, various kinds of tetradecenyl groups, various
kinds of pentadecenyl groups, various kinds of hexadecenyl groups, various kinds of
heptadecenyl groups, various kinds of octadecenyl groups, various kinds of nonadecenyl
groups, various kinds of icosenyl groups, various kinds of heneicosenyl groups, various
kinds of docosenyl groups, and various kinds of tricosenyl groups. Preferable examples
thereof include various kinds of pentadecyl groups, various kinds of heptadecyl groups,
various kinds of nonadecyl groups, various kinds of heneicosanyl groups, various kinds
of pentadecenyl groups, various kinds of heptadecenyl groups, various kinds of nonadecenyl
groups, and various kinds of heneicosenyl groups. More preferable examples thereof
include various kinds of pentadecyl groups, various kinds of heptadecyl groups, various
kinds of pentadecenyl groups, and various kinds of heptadecenyl groups. Here, the
term "various kinds" indicates to include the above shown straight chain or the above
shown branched chain.
[0011] In the formula (I), R
3 and R
4 represent a hydrocarbon group having 1 to 4 carbon atoms preferably represent an
alkyl group particularly preferably represent a methyl group. In the formula (I),
k and l may be the same as or different from each other and respectively represent
an integer of 5 to 10, preferably an integer of 5 to 8, more preferably an integer
of 5 to 7, particularly preferably an integer of 5 or 6. X
- represents an anion which is selected from the anions suitable for softeners. Examples
of anions include halogen such as chlorine, bromine, and iodine; and ions such as
methylsulfuric acid and ethyl sulfuric acid. Particularly, chloride ion and methylsulfuric
acid ion are preferred.
<Quaternary ammonium salt (II) >
[0012] The softener composition of the present invention may contain the quaternary ammonium
salt (II) represented by the formula (II) together with the quaternary ammonium salt
(I). The content of both of the quaternary ammonium salt (I) and the quaternary ammonium
salt (II) gives excellent softness on fibrous products, which is preferable. As for
R
5 and R
6 in the formula (II), those exemplified by R
1 and R
2 in the formula (I) may be used and preferable examples thereof may be used. As for
R
7 and R
8 in the formula (II), those exemplified by R
3 and R
4 in the formula (I) may be used and preferable examples thereof may be used. As for
X'
- in the formula (II), one exemplified by X
- in the formula (I) may be used and preferable examples thereof may be used. m and
n may be the same as or different from each other and respectively represent an integer
of 2 or 3.
<Softener composition>
[0013] The content of the quaternary ammonium salt (I) in the softener composition of the
present invention is preferably from 1 to 40% by weight, preferably from 2 to 30%
by weight, more preferably from 3 to 20% by weight, more preferably from 4 to 10%
by weight, particularly preferably from 5 to 8% by weight. When the content of the
quaternary ammonium salt (I) is 1% by weight or more, higher performance may be achieved.
Meanwhile, the blending amount is 40% by weight or less, solution stability is more
excellent, thereby making the production easy.
[0014] When the softener composition of the present invention contains the quaternary ammonium
salt (I) and the quaternary ammonium salt (II), it may give higher softness as described
above.
[0015] When the softener composition contains the quaternary ammonium salt (II), the total
content of the quaternary ammonium salt (I) and the quaternary ammonium salt (II)
in the softener composition is preferably larger than 1% by weight and 40% by weight
or less, more preferably from 2 to 15% by weight. The weight ratio of the quaternary
ammonium salt (I) and the quaternary ammonium salt (II) is preferably 99:1 to 50:50
(the quaternary ammonium salt (I): the quaternary ammonium salt (II)), more preferably
80:20 to 55:45, particularly preferably 70:30 to 55:45. As for the weight ratio, when
the ratio of the quaternary ammonium salt (II) is 50 or less, the composition is excellent
in water absorption and handling properties.
[0016] The softener composition of the present invention contains water. Usually, the balance
of the composition is water. The pH of the softener composition of the present invention
at 20°C is preferably from 1.5 to 6. From the viewpoint of preservation and sterilizing
properties, low pH is preferred. Too low a pH may cause decomposition of components
which are usually blended in the composition. Therefore, the pH is more preferably
from 1.5 to 5, further preferably from 2 to 4.5. In order to adjust the pH, any inorganic
or organic acids and alkali may be used. Specific examples thereof include carboxylic
acids such as hydrochloric acid, sulfuric acid, phosphoric acid, dialkyl sulfuric
acid, alkyl sulfuric acid, dialkyl carbonic acid, paratoluenesulfonic acid, acetic
acid, citric acid, malic acid, succinic acid, lactic acid, and glycolic acid; polymeric
acrylic acid such as acrylic acid, hydroxy ethane diphosphonic acid, tripoliphosphoric
acid, phytic acid; short-chain amine compounds such as ethylenediaminetetraacetic
acid, triethanolamine, diethanolamine, dimethylamine, N-methylethanolamine, N-methyldiethanolamine,
N-methyl-N-(2-hydroxyethyl)-N-(2-cyanoethyl)amine, N-methyl-N-(2-hydroxyethyl)propanediamine,
2,3-dihydroxy-N,N-dimethylpropylamine, N,N-di(2-hydroxyethyl)propanediamine; or alkylene
oxide adducts thereof, long-chain amine compounds having 8 to 36 carbon atoms being
bonded to nitrogen, or alkylene oxide adducts thereof. The above-described salts may
also be used. Alkali metal hydroxide, alkali metal carbonate, alkali metal silicate
or the like may be used. Among them, hydrochloric acid, methylsulfuric acid, sodium
hydroxide, diethanolamine, and triethanolamine are preferred. The present invention
further contains at least one selected from components (c-1) and (c-2) as component
(c) so that the preserving and sterilizing property of the composition may be improved.
[0017] The component (c-1) is an alcohol having 1 to 8 carbon atoms. Specific examples thereof
include ethanol, isopropanol, propylene glycol, diethylene glycol, dipropylene glycol,
1,2-pentanediol, hexylene glycol, trimethylpentanediol, benzyl alcohol, diethylene
glycol monobutyl ether, 2-phenoxyethanol, and 2-phenylethanol. Among them, compounds
not containing a nitrogen atom, such as ethanol, isopropanol, propylene glycol, 1,2-pentanediol,
hexylene glycol, benzyl alcohol, diethylene glycol monobutyl ether, and 2-phenoxyethanol
are preferred. Two or more of these may be combined for use. The blending amount of
the component (c-1) in the composition is preferably from 0.1 to 60% by weight, more
preferably from 1 to 40% by weight, particularly preferably from 1 to 25% by weight.
As for a lower alcohol, alcohols modified by modifying agents such as denatonium benzoate,
8-acetylated sucrose, brucine, orange, and citrus may be used.
[0018] The component (c-2) is a compound selected from benzoic acids and phenol compounds.
Examples thereof include benzoic acid or a salt thereof, salicylic acid or a salt
thereof, para-hydroxybenzoic acid or a salt thereof, methyl parahydroxybenzoate, ethyl
para-hydroxybenzoate, propyl parahydroxybenzoate, butyl parahydroxybenzoate, benzyl
parahydroxybenzoate, 3-methyl-3-isopropylphenol, o-phenylphenol, 2-isopropyl-5-methylphenol,
resorcin, cresol, and 2,6-di-tert-butyl-p-cresol. Among them, benzoic acid and 2,6-di-tert-butyl-p-cresol
are preferred. One or two or more of these may be combined for use. The blending amount
of the component (c-2) in the composition is preferably from 0.0001 to 5% by weight,
more preferably from 0.0003 to 3% by weight, particularly preferably from 0.0005 to
1% by weight.
[0019] The softener composition of the present invention has excellent handling properties.
In order to further improve dispersibility, alkylene oxide adducts of alcohol, amine
or fatty acid may be used. However, it is possible to decrease the added amount more
greatly than a usual amount. The carbon chain of the alkylene oxide adducts of alcohol,
amine or fatty acid may be branched or straight, and may be unsaturated. Further,
the carbon chain may have distribution. The carbon chain has preferably 6 to 20 carbon
atoms, more preferably 8 to 18 carbon atoms. When the carbon chain is straight, the
carbon chain has preferably 6 to 14 carbon atoms, more preferably 8 to 12 carbon atoms,
even more preferably 8 to 10 carbon atoms. When the carbon chain is branched, the
carbon chain has preferably 6 to 17 carbon atoms, more preferably 9 to 17 carbon atoms,
and even more preferably 13 carbon atoms. As a raw material, Exxal (manufactured by
Exon Chemicals), Lutensol TO (manufactured by BASF), Oxocol C13 (manufactured by Kyowa
Hakko Kirin Co., Ltd.) or the like may be used. Particularly, in the case of the alkylene
oxide adduct of an alcohol, a primary or secondary alcohol may also be used. The primary
alcohol provides a resulting composition with a good dispersibility of the blended
components. Alcohol having 13 carbon atoms is produced from a raw material of dodecen.
The starting material thereof may be butylene or propylene. When the carbon chain
contains an unsaturated group, the carbon chain having 18 carbon atoms is preferred.
The stereoisomer structure of the unsaturated group may be a cis- or trans-isomer
or a mixture thereof. Particularly, the ratio of the cis- or trans-isomer is preferably
25/75 to 100/0 (weight ratio). Alkylene oxide is preferably ethyleneoxide (EO), and
propylene oxide (PO) or butylene oxide (BO) may be added together with ethyleneoxide.
The average addition mole number of EO is from 10 to 100 mol, preferably from 20 to
80 mol, particularly preferably from 30 to 60 mol. The average addition mole mumber
of PO or BO to be added together with EO is from 1 to 5, preferably from 1 to 3. In
this case, PO or BO may be added after addition of EO or EO may be added after addition
of PO or BO. Examples thereof include an adduct having 9 moles on the average of EO
and 1 mole on the average of PO, added to nonyl alcohol, an adduct having 40 moles
on the average of EO, added to primary isononyl alcohol, an adduct having 20 moles
on the average of EO, added to primary isodecyl alcohol, an adduct having 20 moles
on the average of EO, added to lauryl alcohol, an adduct having 60 moles on the average
of EO, added to primary isohexadecyl alcohol, an adduct having 40 moles on the average
of EO, added to primary isotridecyl alcohol, an adduct having 60 moles on the average
of EO, added to beef tallow alkylamine, an adduct having 60 moles on the average of
EO, added to beef tallow alkylamine, an adduct having 50 moles on the average of EO,
added to oleylamine, and an adduct having 20 moles on the average of EO, added to
lauric acid. Usable examples thereof include Emalex series (manufactured by NIHON
EMULSION Co., Ltd.), Emulmin series (manufactured by Sanyo Chemical Industries, Ltd.),
TDA series and Esomin series (manufactured by Lion Corporation.), Softanol series
such as Softanol 300 (manufactured by NIPPON SHOKUBAI CO., LTD.), and Lutensol series
(manufactured by BASF). The blending amount of the alkylene oxide adducts of alcohol,
amine or fatty acid is preferably from 0 to 5% by weight, more preferably from 0 to
2% by weight, particularly preferably from 0 to 1% by weight based on the whole composition.
[0020] The softener composition of the present invention has low viscosity and excellent
handling properties. In order to further decrease the viscosity of the composition,
inorganic or organic salts [excluding the quaternary ammonium salts (I) and (II)]
may be used in a small amount. Among these inorganic or organic salts, an alkali metal
salt or an alkaline earth metal salt is preferred. Specific examples thereof include
sodium chloride, potassium chloride, calcium chloride, magnesium chloride, aluminium
chloride, sodium sulfate, magnesium sulfate, potassium sulfate, sodium nitrate, magnesium
nitrate, sodium p-toluenesulfonate, sodium glycolate, sodium acetate, potassium acetate,
potassium glycolate and sodium lactate. Calcium chloride and magnesium chloride are
preferred. These blending amounts allow the usual amount to be reduced greatly and
they are set to preferably 0 to 2% by weight, more preferably 0.001 to 1% by weight,
further preferably 0.01 to 0.5% by weight. The ratio of these inorganic or organic
salts is preferably from 0.001 to 10% by weight, more preferably from 0.005 to 5%
by weight, particularly preferably from 0.05 to 1% by weight based on the content
of the quaternary ammonium salt (I) in the softener composition or the total content
of the quaternary ammonium salt (I) and the quaternary ammonium salt (II).
[0021] When the softener composition of the present invention is used for fibrous products
such as clothes, silicone selected from dimethylpolysiloxane and modified-dimethylpolysiloxane
having various kinds of organic functional groups may be used alone or as a mixture
of two or more kinds thereof at an arbitrary ratio in order to give tightness and
improve ironing smoothness. When silicone is dimethylpolysiloxane, the degree of polymerization
of silicone is preferably in the range of 10 to 1,000,000 mPa·s, more preferably in
the range of 10 to 100,000 mPa·s, even more preferably in the range of 10,000 to 100,000
mPa·s. When silicone is a modified dimethylpolysiloxane, examples thereof include
silicones produced by modifying two or more of organic functional groups such as amino,
amide, alkyl, aralkyl, carboxyl, fluoroalkyl, higher alcohol ester, polyether, epoxy,
carbinol, mercapto, phenol, methacrylic, aminopolyether, amidopolyether, and alkyl
alcohol. One or two or more thereof are selected. The bonding position of the organic
functional group to the main chain of dimethylpolysiloxane may be the side chain or
the end. When the organic functional group is bonded to the end, it may be bonded
to either one end or both ends. The weight ratio of the organic functional group to
dimethylpolysiloxane may be optional and is not particularly limited. As the modified-dimethylpolysiloxane,
dimethylpolysiloxane hydride, which is a precursor for introducing an organic functional
group, or hydroxylated dimethylpolysiloxane may be independently used. Alternatively,
they may be mixed with a modified-dimethylpolysiloxane having an organic functional
group. Preferable examples of silicones include dimethyl silicone, polyoxyethylene-modified-silicone,
silicone containing a hydrogen group or a hydroxyl group, and the emulsified products
thereof. The blending ratio of these silicone compounds in the composition may be
preferably from 0.1 to 20% by weight, more preferably from 0.3 to 10% by weight.
[0022] In order to improve preservation and sterilizing properties, at least one of the
following compounds maybe used preferably in an amount of 0 to 0.5% by weight, more
preferably 0 to 0.1% by weight based on the amount of the composition: sodium pyrithione,
1,3-bis(hydroxymethyl)-5,5-dimethyl-2,4-imidazolidinedione, dimethylol dimethylhydantoin,
DMDM hydantoin (manufactured by Lonza or Glydant Plus); N-[1,3-bis(hydroxymethyl)-2,5-dioxo-4-imidazolidinyl]-N,N'-bis(hydroxymethyl)urea
(generally marketed under the name of diazolidinyl urea); N,N'-methylene-bis{N'-[1-(hydroxymethyl)-2,5-dioxo-4-imidazolidinyl]urea};
imidazolidinedione compounds generally known as imidazolidinyl urea; polymethoxide
bicyclic oxazolidine compounds; low-molecular-weight aldehydes such as formaldehyde
and glutaraldehyde; polyaminopropylbiguanide known as polyhexamethylene biguanide
having formula: HCl NH
2-(CH
2)
3-[-(CH
2)
3-NH-C(=NH)-NH-C(=NH·HCl)-NH-(CH
2)
3-]
x-(CH
2)
3-NH-C(=NH)-NH-CN; 1,1'-hexamethylene-bis (5- (p-chlorophenyl)biguanide generally known
as chlorhexidine; acetic acid, digluconic acid, digluconate (i.e., salt) and diacetates
thereof, commercially available products such as Proxel IB, manufactured by Avecia
Ltd.; 1-(3-chloroallyl)-3,5,7-triaza-1-azoniaadamantane chloride, for example, marketed
under the trade name of Dowicil200 from Dow Chemical; dehydroacetic acid, 4,4'-diamidino-α,ω-diphenoxypropane
diisethionate generally known as propamidine isethionate; 4,4'-diamidino-α,ω-diphenoxyhexane
diisethionate generally known as hexamidine isethionate; imidazole- or thiazole-based
antibacterial agents such as 12- (4' -thiazolyl) -benzimidazole, 2-(4-thiocyanomethylthio)benzothiazole,
and methyl-2-benzimidazole carbamide; 1,1,1-trichloro-2-methylpropan-2-ol, chlorobutanol
generally known as chlorobutanol, 4,4'-(trimethylenedioxy)-bis-(3-bromobenzamidine)diisethionate,
or dibromopropamidine; 3,4,4'-trichlorocarbanilide or N-(4-chlorophenyl)-N'-(3,4-dichlorophenyl)urea
which is known as trichlocarban; 2,4,4'-trichloro-2'-hydroxydiphenylether (generally
known as triclosan); and the like.
[0023] In order to make a user know use of a product, perfumes may be used. One or two or
more of the following components may be mixed for use: hydrocarbons generally used
for softener compositions, such as aliphatic hydrocarbon, terpene hydrocarbon, and
aromatic hydrocarbon; alcohols such as aliphatic alcohol, terpene alcohol, and aromatic
alcohol; ethers such as aliphatic ether and aromatic ether; oxides such as aliphatic
oxide and oxides of terpenes; aldehydes such as aliphatic aldehyde, terpene-based
aldehyde, hydrogenated aromatic aldehyde, and thioaldehyde, aromatic aldehyde; ketones
such as aliphatic ketone, terpene ketone, hydrogenated aromatic ketone, aliphatic
cyclic ketone, non-benzene-based aromatic ketone, and aromatic ketone; acids such
as acetals, ketals, phenols, ether phenols, fatty acid, terpene-based carboxylic acid,
hydrogenated aromatic carboxylic acid, and aromatic carboxylic acid; lactones such
as acid amides, aliphatic lactone, macrocyclic lactone, terpene-based lactone, hydrogenated
aromatic lactone, and aromatic lactone; esters such as aliphatic ester, furan-based
carboxylic acid ester, aliphatic cyclic carboxylic acid ester, cyclohexyl carboxylic
acid ester, terpene-based carboxylic acid ester, and aromatic carboxylic acid ester;
synthetic perfumes such as nitrogen-containing compounds, for example, nitro musks,
nitrile, amine, pyridines, quinolines, pyrrole, and indole; natural perfumes from
animals and plants; and prepared perfumes containing the natural perfumes and/or synthetic
perfumes. Usable examples thereof include perfumes described in "
Synthetic Perfume, Chemistry and Knowledge on products", Motoichi Indo, The Chemical
Daily Co., Ltd., 1996 and "
Perfume and Flavor Chemicals", STEFFEN ARCTANDER, MONTCLAIR, N.J. 1969.
[0024] In order to improve the appearance of the composition, at least one water-soluble
dye selected from an acid dye, a direct dye, a basic dye, a reactive dye, a mordant
dye, and an acid mordant dye may be added. Specific examples of the dye to be added
are described in
Dye handbook manual (edited by Society of Synthetic Organic Chemistry, Japan, Maruzen,
issued on July 20, 1970).
[0025] In addition to the above-described components, known components which are blended
with usual softener compositions may be added to the softener composition of the present
invention as other optional components in a range not impairing the effect of the
invention. Examples of optional components include di-long-chain alkyldimethyl quaternary
ammonium salt, mono-long-chain alkyltrimethyl quaternary ammonium salt; higher fatty
acids such as stearic acid, oleic acid, and palmitic acid; fatty acid methyl esters
such as stearic acid methyl ester, oleic acid methyl ester, palmitic acid methyl ester
which are esters of the lower alcohols thereof preferably in an amount of 0 to 2%
by weight; nonionic surfactants such as fatty acid glycerol ester which is ester of
stearic acid, glycerin or pentaerythritol preferably in an amount of 0 to 1.0% by
weight; higher alcohols such as stearyl alcohol, palmityl alcohol, oleyl alcohol,
and primary or secondary isotridecyl alcohol preferably in an amount of 0 to 3.0 %
by weight; low-temperature stabilizers such as ethylene glycol and glycerin preferably
in an amount of 0 to 10% by weight; hydroxy ethane diphosphonic acid (Feliox CY-115,
manufactured by Lion Corporation); ethylenediaminetetraphosphonic acid (Dequest2041,
manufactured by Monsanto); phosphonic-type chelating agents such as D-2000, 2010,
2066; chelating agents such as ethylenediaminetetraacetic acid, nitrilotriacetic acid,
citric acid, protocatechuic acid , tripoliphosphoric acid, ethylenediamine disuccinic
acid, methylglycinediacetic acid, iminodisuccinic acid, hydroxyiminodisuccinic acid,
aspartic acid, polyglyoxylic acid, polyaspartic acid, polyacrylic acid, copolymer
of acrylic acid and maleic acid (the molecular weight of polymer is arbitrary) and
salts thereof such as sodium preferably in an amount of 0 to 5.0%; antioxidants preferably
in an amount of 0 to 0.1% by weight; hydrocarbons which are liquid at ordinary temperature,
such as liquid paraffin preferably in an amount of 0.01 to 2.0% by weight; ureas,
pigments, cellulose derivatives, ultraviolet absorbers, and fluorescent brighteners.
[0026] The usable concentration of the composition of the present invention varies depending
on the application and the form to be used. When the composition of the present invention
is used for fibrous products such as clothes, the composition is preferably diluted
so that the concentration of the composition of the present invention to rinsing water
is from 0.001 to 3% by weight, preferably from 0.01 to 1% by weight.
<Method for producing softener composition>
[0027] The softener composition of the present invention may be produced by the method for
producing a softener composition including the steps 1 and 2:
step 1: producing bis(polyalkoxyalkanol)alkylamine by a reaction of halopoly alkoxy
alkanol with amine represented by the following formula (III):
R3-NH2 (III)
[wherein R3 represents a hydrocarbon group having 1 to 4 carbon atoms.]; and
step 2: esterifying bis (polyalkoxyalkanol) alkylamine produced in the step 1 with
fatty acids or the derivatives thereof and quaternizing the ester.
[0028] This method allows for an efficient production of a quaternary ammonium salt having
an oxyethylene chain without the EO distribution which is the quaternary ammonium
salt (I).
[0029] In the step 1, bis(polyalkoxyalkanol)alkylamine is produced by a reaction of halopoly
alkoxy alkanol with amine represented by the formula (III).
[0030] As halopoly alkoxy alkanol to be used in the step 1, halopoly alkoxy alkanol represented
by the following formula (IV) is listed.
Y(CH
2CH
2P)
iH (IV)
[wherein Y represents a halogen atom and i represents an integer of 5 to 10.]
[0031] Specific examples of the compound represented by formula (IV) include polyoxyethylene
[in the formula (IV), i represents 4.], 2-chloroethanol, polyoxyethylene [in the formula
(IV), i represents 5.], and 2-chloroethanol.
[0032] In the step 1, 0.3 to 2 equivalents, preferably 0.4 to 1.8 equivalents of halopoly
alkoxy alkanol (i.e., halopoly alkoxy alkanol/amine) is used based on the amine represented
by the formula (III). In the step 1, water and an alcohol such as ethanol may be used
as a reaction solvent. The reaction temperature in the step 1 is from 70 to 110°C,
preferably from 80 to 100°C. The reaction time is preferably from 1 to 5 hours.
[0033] In the step 1, bis(polyalkoxyalkanol)alkylamine or bis (polyalkoxyalkanol)hydroxyalkylamine
is obtained at a high yield by using the two-stage reaction below.
[0034] The first stage: Amine represented by the formula (III) is reacted with 0.3 to 0.6
equivalent of halopoly alkoxy alkanol (preferably, at 90 to 110 °C, for 1 to 5 hours),
followed by neutralization and removal of salt.
[0035] The second stage: Thereafter, 0.5 to 0.9 equivalent of halopoly alkoxy alkanol to
mono- (polyalkoxyalkanol) is further added to the obtained mixture of di-(polyalkoxyalkanol)
and mono-(polyalkoxyalkanol), which is reacted in water or an alcohol at 70 to 90°C
for 1 to 3 hours, followed by distillation.
[0036] The quaternary ammonium salt (II) may be produced in the same manner as the quaternary
ammonium salt (I) by performing the step 3 of producing bis(polyalkoxyalkanol)alkylamine
or bis(polyalkoxyalkanol)hydroxy alkylamine by a reaction of halopoly alkoxy alkanol,
preferably halopoly alkoxy alkanol represented by the following formula (V), with
amine represented by the formula (III) and the step 4 of esterifying bis(polyalkoxyalkanol)alkylamine
or bis (polyalkoxyalkanol) hydroxyalkylamine which are produced by the step 3 with
fatty acid or a derivative thereof and quaternizing the ester. Therefore, as for the
softener composition containing the quaternary ammonium salt (II), the above-described
steps may be used as steps 3 and 4 for producing the quaternary ammonium salt (II),
in addition to the steps 1 and 2.
Y'(CH
2CH
2O)
jH (V)
[wherein Y' represents a halogen atom and j represents an integer of 2 or 3.]
[0037] Specific examples of the compound represented by formula (V) include 2-(2-chloroethoxy)ethanol,
polyoxyethylene [in the formula (V), j is 2], and 2-chloroethanol.
[0038] Excessive amounts of halopoly alkoxy alkanol and unreacted amine may be removed by
purifying them by distillation or the like.
[0039] In the step 2 or 4, bis(polyalkoxyalkanol)alkylamine or bis(polyalkoxyalkanol)hydroxyalkylamine
(hereinafter referred to as intermediate amine) obtained in the step 1 or 3 is esterified
with fatty acid or the derivatives thereof and then quaternized with alkyl halide.
[0040] In the esterification, higher fatty acid having 12 to 24 carbon atoms, preferably
16 to 22 carbon atoms, more preferably 16 to 18 carbon atoms or the derivatives thereof
are used. Specific examples thereof include fatty acids obtained by purification,
hydrogenation or partial hydrogenation of higher fatty acids such as myristic acid,
palmitic acid, palmitoleic acid, stearic acid, oleic acid, linoleic acid, linolenic
acid; and natural oils and fats such as beef tallow, lard, palm oil, and soybean oil.
The derivatives of fatty acids are alkyl ester of the fatty acid, acid chloride, and
acid anhydride.
[0041] In either the step 2 and the step 4, as for esterification conditions, the molar
ratio of intermediate amine to fatty acid or the derivatives thereof is preferably
1:2 to 1:2.2 (intermediate amine:fatty acid or the derivatives thereof). In the esterification
reaction, neither a solvent nor a catalyst is usually used. The temperature of the
esterification reaction is preferably from 160 to 220°C. The progress and termination
of esterification reaction may be confirmed by reduction of the hydroxyl value of
amines or reduction of the acid number of fatty acids.
[0042] The obtained ester is quaternized after the esterification. When quaternizing, a
usual method for reacting quaternizing agents such as alkyl halide (methyl chloride
etc.) and alkylsulfuric acid may be used. In this regard, a quaternizing agent having
a hydrocarbon group having 1 to 4 carbon atoms which may have a hydroxyl group is
used.
[0043] A mixture containing the quaternary ammonium salt (I) is produced in the steps 1
and 2, while a mixture containing the quaternary ammonium salt (II) is produced in
the steps 3 and 4. These mixtures may be suitably purified by a usual method such
as crystallization. The softener composition of the present invention may be produced
by using the quaternary ammonium salt (I) obtained in such a manner and the quaternary
ammonium salt (II) of the softener composition of the present invention as a blending
component.
EXAMPLES
[0044] The present invention will be described with reference to the following examples.
The examples will not limit the present invention, just exemplifying the invention.
Preparation example 1
[0045] 34 g of 41% monomethylamine solution, 62 g of 2-(2-(2-(2-(2-(2-chloro)ethoxy)ethoxy)ethoxy)ethoxy)ethoxyethanol
[in the formula (IV), i is a compound having an integer of 6], and 80 g of water were
introduced into a pressure-proof reaction vessel and were reacted at 110°C for 4 hours,
a sodium hydroxide solution (equivalent to a chloromer content) was added thereto,
and the produced hydrochloric acid was neutralized. The reaction mixture was transferred
to another reaction vessel and 27 g of chloromer -2-(2-(2-(2-(2-(2-chloro)ethoxy)ethoxy)ethoxy)ethoxy)ethoxyethanol
[in the formula (IV), i is a compound having an integer of 6] was added thereto and
was reacted at 80°C for 1 hour. Thereafter, a sodium hydroxide solution in an amount
equivalent to chloromer-2-(2-(2-(2-(2-(2-chloro)ethoxy)ethoxy)ethoxy)ethoxy)ethoxyethanol,
which had been added, was added dropwise over 30 minutes. After aging for 30 minutes,
the removal of solvent and salt was performed. Then, dimer-(bis(2-(2-(2-(2-(2-ethoxy)ethoxy)ethoxy)ethoxy)ethoxyethanol)methylamine)
was isolated by distillation. The product was confirmed by NMR. Then, 37 g of the
obtained dimer was reacted with 59 g of methyl stearate at 155°C and 20 Torr (2.7
kPa) for 24 hours. After the completion of the reaction, an excessive amount of methyl
stearate was removed by topping and a diesterified product of bis(2-(2-(2-(2-(2-ethoxy)ethoxy)ethoxy)ethoxy)ethoxyethanol)methylamine
was obtained. Subsequently, 51 g of the diesterified product thus obtained was dissolved
in 84 g of isopropyl alcohol and was charged into a pressure-proof vessel. Then, 13
g of methyl chloride was added thereto and the mixture was reacted at 88°C for 5.5
hours to quaternize it. The reaction mixture was crystallized in cold acetone and
dried to obtain the quaternary ammonium salt represented by the formula (I). The products
was identified with NMR and analysis of oils and fats. The structure of the quaternary
ammonium salt is shown in Table 1.
Preparation example 2 (comparative)
[0046] A quaternary ammonium salt of Preparation example 2 was synthesized in the same manner
as Preparation example 1 except that methyldiethanolamine was used in place of bis(2-(2-(2-(2-(2-ethoxy)ethoxy)ethoxy)ethoxy)ethoxyethanol)methylamine.
The structure of the quaternary ammonium salt is shown in Table 1.
Preparation example 3 (comparative)
[0047] Cation of Preparation example 3 was synthesized in the same manner as Preparation
example 1 except that 2-(2-chloroethoxy) ethanol [in the formula (V), j is a compound
having an integer of 2] was used in place of 2-(2-(2-(2-(2-(2-chloro)ethoxy)ethoxy)ethoxy)ethoxy)ethoxyethanol.
The structure of the quaternary ammonium salt is shown in Table 1.
Preparation example 4 (comparative, as per WO 01/02338)
[0048] Cation of Preparation example 4 was synthesized in the same manner as Preparation
example 1 except that 2-(2-(2-chloro)ethoxy)ethoxy)ethanol [in the formula (V), j
is a compound having an integer of 3] was used in place of 2-(2-(2-(2-(2-(2-chloro)ethoxy)ethoxy)ethoxy)ethoxy)ethoxyethanol.
The structure of the quaternary ammonium salt is shown in Table 1.
Preparation example 5
[0049] 34 g of 41% monomethylamine solution, 53 g of 2-(2-(2-(2-(2-chloro)ethoxy)ethoxy)ethoxy)ethoxyethanol
[in the formula (IV), i is a compound having an integer of 5], and 80 g of water were
introdcued into the pressure-proof reaction vessel and were reacted at 110°C for 4
hours, a sodium hydroxide solution (equivalent to a chloromer content) was added thereto,
and the produced hydrochloric acid was neutralized. The reaction mixture was transferred
to another reaction vessel and 23 g of chloromer-2-(2-(2-(2-(2-chloro)ethoxy)ethoxy)ethoxy)ethoxyethanol
[in the formula (IV), i is a compound having an integer of 5] was added thereto and
the mixture was reacted at 80°C for 1 hour. Thereafter, a sodium hydroxide solution
in an amount equivalent to chloromer-2-(2-(2-(2-(2-chloro)ethoxy)ethoxy)ethoxy)ethoxyethanol,
which had been added, was added dropwise over 30 minutes. After aging for 30 minutes,
the removal of solvent and salt was performed, and then dimer-(bis(2-(2-(2-(2-ethoxy)ethoxy)ethoxy)ethoxyethanol)methylamine)
was isolated by distillation. The product was confirmed by NMR. Then, 40 g of the
obtained dimer was reacted with 75 g of methyl stearate at 155°C and 20 Torr (2.7
kPa) for 24 hours. After the completion of the reaction, an excessive amount of methyl
stearate was removed by topping and a diesterified product of bis(2-(2-(2-(2-ethoxy)ethoxy)ethoxy)ethoxyethanol)methylamine
was obtained. Subsequently, 60 g of the diesterified product thus obtained was dissolved
in 84 g of isopropyl alcohol and was charged into a pressure-proof vessel. Then, 10
g of methyl chloride was added thereto and the mixture was reacted at 88°C for 5.5
hours to quaternize it. The reaction mixture was crystallized in cold acetone and
dried to obtain the quaternary ammonium salt represented by the formula (I). The identification
of the products was performed by NMR and analysis of oils and fats. The structure
of the quaternary ammonium salt is shown in Table 1.
Example 1
[0050] The quaternary ammonium salt and calcium chloride obtained in Preparation example
1, having a composition of Table 1, were dispersed in ion exchange water to produce
a liquid softener composition.
Example 2
[0051] The quaternary ammonium salt obtained in Preparation example 1 and the quaternary
ammonium salt and calcium chloride obtained in Preparation example 3, having a composition
of Table 1, were dispersed in ion exchange water to produce a liquid softener composition.
Example 3
[0052] The quaternary ammonium salt and calcium chloride obtained in Preparation example
5, having a composition of Table 1, were dispersed in ion exchange water to produce
a liquid softener composition.
Comparative examples 1 to 3
[0053] Liquid softener compositions were produced in the same manner as Example 1 except
that the quaternary ammonium salts obtained in Preparation examples 2 to 4 were used.
(Evaluation)
(1) Dispersibility and handling properties
[0054] Dispersibility was evaluated based on easiness of preparation of dispersion liquid
and the thickened condition after the preparation was observed. A composition which
was not thickened even in a cooled state after the preparation was judged as being
excellent in handling properties.
(2) Softness and water absorption
[0055] Commercially available cotton towels (T. W220, white, manufactured by Takei Towel
Co., Ltd.) were washed repeatedly 5 times using a commercially available detergent
(trademark: Attack, manufactured by Kao Corporation) to remove the starch of the clothes.
The towels were stirred in tap water at 20°C for 5 minutes using 0.1% by weight of
the liquid softener with the composition of Table 1 (by weight to a towel) so as to
have a bath ratio of 30 L/kg (by weight of a towel). Those towels were dried in a
constant temperature and humidity room at 25°C and 40%RH for 24 hours. Evaluation
of softness and water absorption was performed on respective towels in accordance
with the following evaluation criteria. The results are shown in Table 2.
(Softness)
[0056] The liquid softener composition of Comparative example 1 was used as a control (standard)
and was compared with other bases. The softness was evaluated by the following evaluation
criteria:
+1: Slightly softer than the control;
0: Same as the control; and
-1: The control is slightly softer.
(Water absorption)
[0057] Each of the cotton towels (T. W220, white, manufactured by Takei Towel Co., Ltd.)
was subjected to the above-described treatment and humidity-conditioned in a constant
temperature and humidity room at 25°C/40%RH. A 2.5 cm × 25 cm square test cloth was
cut out from the plain-weave portion of each of the towels. The lower end of the test
cloth was dipped into water at 25°C. After 15 minutes, the height where the water
was spread up in the cloth was measured.

1. A softener composition, comprising a quaternary ammonium salt represented by formula
(I):

wherein R
1 and R
2 may be the same as or different from each other and represent a hydrocarbon group
having 11 to 23 carbon atoms, R
3 and R
4 may be the same as or different from each other and represent a hydrocarbon group
having 1 to 4 carbon atoms, k and l may be the same as or different from each other
and represent an integer of 5 to 10 and X
- represents an anion.
2. The softener composition according to claim 1,
further comprising a quaternary ammonium salt represented by formula (II):

wherein R
5 and R
6 may be the same as or different from each other and represent a hydrocarbon group
having 11 to 23 carbon atoms, R
7 and R
8 may be the same as or different from each other and represent a hydrocarbon group
having 1 to 4 carbon atoms which may have a hydroxyl group, m and n may be the same
as or different from each other and represent an integer of 2 or 3 and X'
- represents an anion.
3. The softener composition according to claim 1 or 2, wherein R1 and R2, being the same as or different from each other, represent a hydrocarbon group having
15 to 17 carbon atoms.
4. The softener composition according to any one of claims 1 to 3, wherein R1 and R2, being the same as or different from each other, represent one selected from pentadecyl
group, heptadecyl group, pentadecenyl group and heptadecenyl group, being a straight
chain or a branched chain.
5. The softener composition according to any one of claims 1 to 4, wherein R1 and R2 is a straight chain heptadecyl group.
6. The softener composition according to any one of claims 1 to 5, wherein R3 and R4 represent methyl group.
7. The softener composition according to any one of claims 1 to 6, wherein k and l, being
the same as or different from each other, represent an integer of 5 to 6.
8. The softener composition according to any one of claims 2 to 7, wherein R5 and R6, being the same as or different from each other, represent a hydrocarbon group having
15 to 17 carbon atoms.
9. The softener composition according to any one of claims 2 to 8, wherein R5 and R6, being the same as or different from each other, represent one selected from pentadecyl
group, heptadecyl group, pentadecenyl group and heptadecenyl group, being a straight
chain or a branched chain.
10. The softener composition according to any one of claims 2 to 9, wherein R5 and R6 is straight chain heptadecyl group.
11. The softener composition according to any one of claims 2 to 10, wherein R7 and R8, being the same as or different from each other, represent one selected from methyl
group or a hydroxyethyl group.
12. The softener composition according to any one of claims 2 to 11, wherein R7 and R8 represent methyl group.
13. The softener composition according to any one of claims 2 to 12, wherein the weight
ratio of the quaternary ammonium salt (I) to the quaternary ammonium salt (II) is
the quaternary ammonium salt (I) : the quaternary ammonium salt (II) of 99:1 to 50:50.
14. The softener composition according to any one of claims 2 to 12, wherein the weight
ratio of the quaternary ammonium salt (I) to the quaternary ammonium salt (II) is
the quaternary ammonium salt (I): the quaternary ammonium salt (II) of 70:30 to 55:45
15. The softener composition according to any one of claims 2 to 14, having a pH of from
2 to 4.5 at 20°C.
16. The softener composition according to any one of claims 2 to 15, wherein the content
of the quaternary ammonium salt (I) in the softener composition is from 5 to 8% by
weight.
17. A method for producing the softener composition according to any one of claims 1 to
16, comprising the following steps 1 and 2 as a step of producing the quaternary ammonium
salt represented by the formula (I):
step 1: producing a bis (polyalkoxyalkanol) alkylamine by a reaction of a halopoly
alkoxy alkanol with an amine represented by the following formula (III):
R3-NH2 (III)
[wherein R3 represents a hydrocarbon group having 1 to 4 carbon atoms]; and
step 2: esterifying the bis(polyalkoxyalkanol)alkylamine produced in the step 1 with
fatty acids or a derivative thereof and quaternizing the ester.
1. Weichmacherzusammensetzung, umfassend ein quaternäres Ammoniumsalz, das durch Formel
(I) gegeben ist:

wobei
R
1 und R
2 gleich oder voneinander verschieden sein können und Kohlenwasserstoffgruppen mit
11 bis 23 Kohlenstoffatomen sind, R
3 und R
4 gleich oder voneinander verschieden sein können und eine Kohlenwasserstoffgruppe
mit 1 bis 4 Kohlenstoffatomen sind, k und 1 gleich oder voneinander verschieden sein
können und eine ganze Zahl von 5 bis 10 sind und X
- ein Anion ist.
2. Weichmacherzusammensetzung gemäß Anspruch 1, die ferner ein quaternäres Ammoniumsalz
umfasst, das durch Formel (II) gegeben ist:

wobei
R
5 und R
6 gleich oder voneinander verschieden sein können und eine Kohlenwasserstoffgruppe
mit 11 bis 23 Kohlenstoffatomen sind, R
7 und R
8 gleich oder voneinander verschieden sein können und eine Kohlenwasserstoffgruppe
mit 1 bis 4 Kohlenstoffatomen, die eine Hydroxylgruppe aufweisen können, sind, m und
n gleich oder voneinander verschieden sein können und eine ganze Zahl von 2 oder 3
sind und X- ein Anion ist.
3. Weichmacherzusammensetzung gemäß Anspruch 1 oder 2, wobei R1 und R2, die gleich oder voneinander verschieden sind, eine Kohlenwasserstoffgruppe mit 15
bis 17 Kohlenstoffatomen sind.
4. Weichmacherzusammensetzung gemäß einem der Ansprüche 1 bis 3, wobei R1 und R2, die gleich oder voneinander verschieden sind, eine Gruppe ausgewählt aus einer Pentadecylgruppe,
Heptadecylgruppe, Pentadecenylgruppe und Heptadecenylgruppe , mit einer geraden Kette
oder einer verzweigten Kette, sind.
5. Weichmacherzusammensetzung gemäß einem der Ansprüche 1 bis 4, wobei R1 und R2 eine Heptadecylgruppe mit gerader Kette sind.
6. Weichmacherzusammensetzung gemäß einem der Ansprüche 1 bis 5, wobei R3 und R4 eine Methylgruppe sind.
7. Weichmacherzusammensetzung gemäß einem der Ansprüche 1 bis 6, wobei k und l, die gleich
oder voneinander verschieden sind, eine ganze Zahl von 5 bis 6 sind.
8. Weichmacherzusammensetzung gemäß einem der Ansprüche 2 bis 7, wobei R5 und R6, die gleich oder voneinander verschieden sind, eine Kohlenwasserstoffgruppe mit 15
bis 17 Kohlenstoffatomen sind.
9. Weichmacherzusammensetzung gemäß einem der Ansprüche 2 bis 8, wobei R5 und R6, die gleich oder voneinander verschieden sind, eine Gruppe ausgewählt aus einer Pentadecylgruppe,
Heptadecylgruppe, Pentadecenylgruppe und Heptadecenylgruppe, mit einer geraden Kette
oder einer verzweigten Kette, sind.
10. Weichmacherzusammensetzung gemäß einem der Ansprüche 2 bis 9, wobei R5 und R6 eine Heptadecylgruppe mit gerader Kette sind.
11. Weichmacherzusammensetzung gemäß einem der Ansprüche 2 bis 10, wobei R7 und R8, die gleich oder voneinander verschieden sind, eine Gruppe ausgewählt aus einer Methylgruppe
oder eine Hydroxyethylgruppe sind.
12. Weichmacherzusammensetzung gemäß einem der Ansprüche 2 bis 11, wobei R7 und R8 eine Methylgruppe sind.
13. Weichmacherzusammensetzung gemäß einem der Ansprüche 2 bis 12, wobei das Gewichtsverhältnis
des quaternären Ammoniumsalzes (I) zum quaternären Ammoniumsalz (II), gemäß quaternäres
Ammoniumsalz (I):quaternäres Ammoniumsalz (II), bei 99:1 bis 50:50 liegt.
14. Weichmacherzusammensetzung gemäß einem der Ansprüche 2 bis 12, wobei das Gewichtsverhältnis
des quaternären Ammoniumsalzes (I) zum quaternären Ammoniumsalz (II), gemäß quaternäres
Ammoniumsalz (I):quaternäres Ammoniumsalz (II), bei 70:30 bis 55:45 liegt.
15. Weichmacherzusammensetzung gemäß einem der Ansprüche 2 bis 14, die einen pH von 2
bis 4,5 bei 20°C aufweist.
16. Weichmacherzusammensetzung gemäß einem der Ansprüche 2 bis 15, wobei der Gehalt des
quaternären Ammoniumsalzes (I) in der Weichmacherzusammensetzung 5 bis 8 Gew.-% beträgt.
17. Verfahren zur Herstellung der Weichmacherzusammensetzung einem der Ansprüche 1 bis
16, das die folgenden Schritte 1 und 2 als einen Schritt zur Herstellung des quaternären
Ammoniumsalzes, das durch die Formel (I) gegeben ist, umfasst:
Schritt 1: Herstellen eines bis-(Polyalkoxyalkanol)alkylamins durch eine Reaktion
eines Halopolyalkoxyalkanols
R3-NH2 (III)
mit einem Amin, das durch die folgende Formel (III) gegeben ist:
[wobei R3 eine Kohlenwasserstoffgruppe mit 1 bis 4 Kohlenstoffatomen ist]; und
Schritt 2: Verestern des bis-(Polyalkoxyalkanol)alkyl-amins, hergestellt im Schritt
1, mit Fettsäuren oder Derivaten davon und Quaternärisieren des Esters.
1. Composition d'adoucissant, comprenant un sel d'ammonium quaternaire représenté par
la formule (I) :

dans laquelle R
1 et R
2 peuvent être identiques ou différents l'un de l'autre et représentent un groupe hydrocarboné
ayant 11 à 23 atomes de carbone, R
3 et R
4 peuvent être identiques ou différents l'un de l'autre et représentent un groupe hydrocarboné
ayant 1 à 4 atomes de carbone, k et l peuvent être identiques ou différents l'un de
l'autre et représentent un nombre entier de 5 à 10 et X
- représente un anion.
2. Composition d'adoucissant selon la revendication 1, comprenant en outre un sel d'ammonium
quaternaire représenté par la formule (II)

dans laquelle R
5 et R
6 peuvent être identiques ou différents l'un de l'autre et représentent un groupe hydrocarboné
ayant 11 à 23 atomes de carbone, R
7 et R
8 peuvent être identiques ou différents l'un de l'autre et représentent un groupe hydrocarboné
ayant 1 à 4 atomes de carbone qui peut avoir un groupe hydroxyle, m et n peuvent être
identiques ou différents l'un de l'autre et représentent un nombre entier de 2 ou
3 et X'
- représente un anion.
3. Composition d'adoucissant selon la revendication 1 ou 2, dans laquelle R1 et R2, qui sont identiques ou différents l'un de l'autre, représentent un groupe hydrocarboné
ayant 15 à 17 atomes de carbone.
4. Composition d'adoucissant selon l'une quelconque des revendications 1 à 3, dans laquelle
R1 et R2, qui sont identiques ou différents l'un de l'autre, représentent un groupe choisi
parmi un groupe pentadécyle, un groupe heptadécyle, un groupe pentadécényle et un
groupe heptadécényle, étant une chaîne linéaire ou une chaîne ramifiée.
5. Composition d'adoucissant selon l'une des revendications 1 à 4, dans laquelle R1 et R2 représentent un groupe heptadécyle à chaîne linéaire.
6. Composition d'adoucissant selon l'une quelconque des revendications 1 à 5, dans laquelle
R3 et R4 représentent un groupe méthyle.
7. Composition d'adoucissant selon l'une quelconque des revendications 1 à 6, dans laquelle
k et l, qui sont identiques ou différents l'un de l'autre, représentent un nombre
entier de 5 à 6.
8. Composition d'adoucissant selon l'une quelconque des revendications 2 à 7, dans laquelle
R5 et R6, qui sont identiques ou différents l'un de l'autre, représentent un groupe hydrocarboné
ayant 15 à 17 atomes de carbone.
9. Composition d'adoucissant selon l'une quelconque des revendications 2 à 8, dans laquelle
R5 et R6, qui sont identiques ou différents l'un de l'autre, représentent un groupe choisi
parmi un groupe pentadécyle, un groupe heptadécyle, un groupe pentadécényle et un
groupe heptadécényle, étant une chaîne linéaire ou une chaîne ramifiée.
10. Composition d'adoucissant selon l'une quelconque des revendications 2 à 9, dans laquelle
R5 et R6 représentent un groupe heptadécyle à chaîne linéaire.
11. Composition d'adoucissant selon l'une quelconque des revendications 2 à 10, dans laquelle
R7 et R8, qui sont identiques ou différents l'un de l'autre, représentent un groupe choisi
parmi un groupe méthyle ou un groupe hydroxyéthyle.
12. Composition d'adoucissant selon l'une quelconque des revendications 2 à 11, dans laquelle
R7 et R8 représentent un groupe méthyle.
13. Composition d'adoucissant selon l'une quelconque des revendications 2 à 12, dans laquelle
le ratio pondéral du sel d'ammonium quaternaire (I) par rapport au sel d'ammonium
quaternaire (II), le sel d'ammonium quaternaire (I) : le sel d'ammonium quaternaire
(II), est de 99:1 à 50:50.
14. Composition d'adoucissant selon l'une quelconque des revendications 2 à 12, dans laquelle
le ratio pondéral du sel d'ammonium quaternaire (I) par rapport au sel d'ammonium
quaternaire (II), le sel d'ammonium quaternaire (I) : le sel d'ammonium quaternaire
(II), est de 70:30 à 55:45.
15. Composition d'adoucissant selon l'une quelconque des revendications 2 à 14, ayant
un pH de 2 à 4,5 à 20 °C.
16. Composition d'adoucissant selon l'une quelconque des revendications 2 à 15, dans laquelle
la teneur en sel d'ammonium quaternaire (I) dans la composition d'adoucissant est
de 5 à 8 % en poids.
17. Procédé de fabrication de la composition d'adoucissant selon l'une quelconque des
revendications 1 à 16, comprenant les étapes 1 et 2 suivantes comme étape de fabrication
du sel d'ammonium quaternaire représenté par la formule (I) :
étape 1 : fabrication d'une bis(polyalcoxyalcanol)alkylamine par réaction d'un halogénopoly
alcoxy alcanol avec une amine représentée par la formule (III) suivante :
R3-NH2 (III)
[dans laquelle R3 représente un groupe hydrocarboné ayant 1 à 4 atomes de carbone] ; et
étape 2 : estérification de la bis(polyalcoxyalcanol)alkylamine produite à l'étape
1 avec des acides gras ou un dérivé de ceux-ci, et quaternisation de l'ester.